Toluene → 1-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

HRID 255562Notes

Reaction equation

HRID 255562 reaction equation
[OH:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O.C1(C)C=CC=CC=1>[Pt].C(O)C>[NH2:15][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:5]=1[NH:4][CH2:3][C:2]([OH:1])([CH3:18])[CH3:19])=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 1140TolueneHCID 139583422-Methyl-1-((3-nitroquinolin-4-yl)amino)propan-2-ol

Product 1

HCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Using the method of Example 26, 7.0 g (0.027 mole) of 4-(2-hydroxy-2-methylpropylamino)-3-nitroquinoline, 1 g of platinum on charcoal, 200 ml of toluene and 150 ml of ethanol was hydrogenated on a Paar apparatus. The solution was filtered, then evaporated to dryness to provide 3-amino-4-(2-hydroxy-2-methylpropylamino)quinoline was a solid residue. To the residue was added 50 ml of triethyl orthoformate and 5 drops of formic acid. The solution was heated at 135° to 140° C. for one hour, then allowed to stand for about 16 hours. The product was separated by filtration, dissolved in hydrochloric acid and reprecipitated with sodium hydroxide solution. The product was recrystallized from ethanol to provide 1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline, m.p. 169°-170° C. Analysis: Calculated for C14H15N3O.H2O: %C, 64.8; %H, 6.6; %N, 16.2; Found: %C, 65.1; %H, 6.6; %N, 16.4.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-a0b7877096a64565be1d3bd67e513b16
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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